Reaktion #730930

Reaktionsgleichung

2-(tert-butyl-dimethyl-silanyloxy)-6-dimethylaminomethylene-cyclohex-2-enone

3-guanidino-benzenesulfonamide

potassium carbonate

→

3-(8-hydroxy-5,6-dihydro-quinazolin-2-ylamino)benzenesulfonamide

Ausbeute 6.5%

Lösungsmittel

DMA

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was evaporated under high vacuum
2. 2
   Sonstigetriturated with dichloromethane (100 mL)
3. 3
   Sonstigeto give a buff
4. 4
   FiltrationThe precipitate was filtered
5. 5
   Einengenthe mother liquors concentrated in vacuo
6. 6
   Sonstigepurified by flash chromatography on silica gel eluting with ethyl acetate

Vorschrift

The crude 2-(tert-butyl-dimethyl-silanyloxy)-6-dimethylaminomethylene-cyclohex-2-enone in DMA (75 mL) was treated with 3-guanidino-benzenesulfonamide as the hydrochloride salt (7.79 g, 31.09 mmol) and potassium carbonate (2.13, g, 15.54 mmol) and the mixture stirred at 110° C. for 20 hours. The mixture was evaporated under high vacuum and triturated with dichloromethane (100 mL) to give a buff coloured precipitate. The precipitate was filtered, the mother liquors concentrated in vacuo and purified by flash chromatography on silica gel eluting with ethyl acetate to give 3-(8-hydroxy-5,6-dihydro-quinazolin-2-ylamino)benzenesulfonamide as a yellow solid (0.63 g, 6.5%). MS (ES+) 319, (ES−) 317. δH (d6 DMSO) 2.04-2.12 (2H, m), 2.66-2.74 (2H, m), 2.84-2.90 (2H, m), 7.33 (2H, s), 7.43 (1H, d), 7.48 (1H, t), 8.16 (1H, d), 8.25 (1H, s), 8.78 (1H, s), 10.25 (1H, s).

Quelle